The principal objectives of this project are to design and execute a total synthesis of the antibiotic cation ionophore A-23187 and related polydentate ligands which will be effective as membrane cation carriers. The rapidly accumulating data which demonstrate that this ionophore is a unique probe for the involvement of metal ions in the control of complex cellular functions justifies the design of more selective membrane ion carriers. Recent studies have suggested that A-23187 and related analogs could be highly useful cardiotonic agents. In studies directly related to the above objectives a new class of chiral spiroketal crown ethers will be synthesized which will hopefully serve as chiral templates for the resolution of racemic alpha-amino acids.